I have a confession. For years I dreaded getting dressed for work, mostly because I thought “polished” and “comfortable” could not live in the same closet. I was wrong, and it took my sister Jenna (who dresses for a corporate job every single day) to prove it to me one rainy Tuesday morning.
She came over with two garment bags and basically hijacked my bedroom. By the end of the morning I had learned more about dressing for the office than I had in the previous decade. And tbh – it was fun. We laughed a lot.
Below are 20 ideas that Jenna and I put together – some for warmer days, some for the deep freeze of January.
20 Looks to Take You From Monday Meetings to Friday Wins
Sculptural Midi Dress With Heels
A midi dress with a bit of structure to it is one of those pieces that does all the heavy lifting for you. You put it on, you add heels, and you are done.
Jenna calls this her “no thinking required” outfit and she wears it on the days she oversleeps. The seaming on a sculptural dress skims the body in a way that feels intentional and pulled together, which is exactly what you want when you are running late and rolling into a 9 am meeting.
Dark-Wash Jeans With Blazer
Here is where I remind you that a good pair of jeans has a place at the office, especially on casual Fridays. A dark-wash pair with a crisp blazer thrown over the top is one of my favorite plus size business casual outfits because it reads as effort without actually requiring much of it.
Choose a blazer with a little shape at the waist. And roll the sleeves. I do not know why the rolled sleeve makes such a difference, but it does.
Faux-Fur Coat With Barrel Jeans
Now we are getting into the cozy territory. A soft faux-fur coat over roomy barrel jeans is the outfit I reach for when it is freezing and I still want to look like I tried.
The coat does most of the talking here. Keep everything underneath simple, a fitted knit and a boot, and let that plush coat be the moment. It is warm, it is a little glamorous, and it makes standing at the bus stop in January far more bearable.
Floral Maxi Dress With Sandals
When spring finally shows up (and it always takes its sweet time), a floral maxi dress with flat sandals is the easiest thing in the world to throw on. One piece. Done.
I wore this on my first day back from a long weekend and got three compliments before lunch. A floral print feels fresh and optimistic, and a maxi length keeps it office-appropriate. Add a thin belt if you want to define the waist, but you do not have to.
Wide-Leg Trousers With Waistcoat
Wide-leg trousers are having a moment and I am so glad, because they are comfortable AND they look expensive. Pair them with a matching or contrasting waistcoat and you have an outfit that feels a bit fashion-forward without trying too hard.
The waistcoat is the secret weapon. It gives structure to the top half while the trousers keep everything breezy below. So chic, so easy.
Straight-Leg Jeans With Loafers
Straight-leg jeans and a good loafer is a combination I fall back on constantly. It is simple, it is classic, and it works with almost any top in your closet.
I will not lie to you, finding the best jeans for plus size women took me a while, but a straight-leg cut with a bit of stretch has become my forever pair. Tuck in a soft sweater, slip on the loafers, and walk out the door.
Funnel-Neck Coat With Knit Dress
On the truly bitter days, a funnel-neck coat over a knit dress is warmth and polish in one. The high funnel neck means you barely need a scarf, which I appreciate because I always lose my scarves.
The knit dress underneath is soft and forgiving and feels almost like wearing your favorite lounge clothes, except no one at the office needs to know that – that is our little secret.
Satin Blouse With Tailored Trousers
A satin blouse tucked into tailored trousers is the outfit for the days you have a big presentation or a lunch with the higher-ups. It just looks important, you know?
The soft sheen of satin catches the light and reads as dressy, while the tailored trousers keep the bottom half sharp. I keep mine in a deep jewel tone because it flatters and photographs well.
Deep-Rinse Jeans With White Shirt
There is something about a deep-rinse jean with a crisp white shirt that will never go out of style. It is fresh, it is clean, it is the outfit equivalent of a deep breath.
Jenna taught me to buy the white shirt a size up so it does not pull anywhere, and then just tuck the front in loosely. It looks relaxed but still put together. And a white shirt somehow makes everything else look more expensive than it is.
Wrap Dress With Statement Earrings
The wrap dress is a classic for a reason. It cinches at the waist, it moves with you, and it feels flattering the second you put it on. Add a pair of statement earrings and you are ready for anything.
I have three of these in rotation. I wear them so much that my husband once asked if I owned any other kind of dress. Fair question, honestly.
Pinstripe Suit With Fitted Knit
A pinstripe suit sounds intimidating but hear me out. Worn with a fitted knit instead of a stiff shirt underneath, it goes from stuffy to modern in a second.
The pinstripe adds a subtle vertical line that feels sharp and professional. And a soft knit underneath keeps the whole thing from feeling like a costume. This is my “I mean business” outfit and I love the confidence it gives me.
Winter-White Jeans With Camel Coat
People are scared of white in winter and I understand why, but winter-white jeans with a camel coat is one of the prettiest combinations there is. So soft, so warm-looking.
Some of the most flattering plus size winter outfits lean into these creamy, warm neutrals instead of the usual black on black on black. A camel coat over off-white denim feels rich and cozy, like a mug of something warm in outfit form.
Pleated Midi Skirt With Blazer
A pleated midi skirt has this lovely swishy movement that makes you feel a little bit fancy just walking down the hall. Pair it with a structured blazer and you balance the softness of the pleats with something sharp.
I like a satiny pleated skirt because it catches the light. It looks dressy but it is honestly as comfortable as a skirt gets. Elastic waistband, no complaints from me.
Barrel-Leg Jeans With Ankle Boots
Barrel-leg jeans are that curved, rounded shape that looks so cool with a little ankle boot peeking out the bottom. It is a trendier silhouette but it works beautifully for the office when the wash is dark enough.
The trick is the boot. A pointed or sleek ankle boot keeps the roomy jean from looking sloppy. My friend Dana wore this to work last week and I immediately texted her asking where the boots were from.
Velvet Midi Dress With Slingbacks
Velvet feels like a treat. A velvet midi dress paired with slingback heels is the outfit for holiday parties at the office, or just for a Wednesday when you want to feel a little luxurious.
The texture of velvet does something magical in low winter light. It looks deep and rich and just slightly festive. And a slingback keeps it grounded and walkable, which matters when you are on your feet all day.
Dark Denim With Tweed Jacket
Dark denim with a tweed jacket is preppy in the best way. It is the outfit that says you read a lot and probably drink your coffee black (even if you actually load it with cream, like I do).
The tweed jacket brings texture and a bit of old-school charm, while the dark denim keeps it from feeling too formal. This is a great transitional look for those in-between weather days when you never know what to expect.
Belted Knit Dress With Tall Boots
A belted knit dress with tall boots is comfort disguised as effort, and I mean that as the highest compliment. You are basically wearing a sweater and boots but you look like you planned it.
The belt defines the waist and the tall boots do the rest. On the coldest mornings, this is what I want to live in. Warm, easy, and it takes about four minutes to put together.
Tailored Jeans With Pointed Flats
Tailored jeans, meaning the kind with a pressed crease down the front, blur the line between denim and trouser. Add pointed flats and you have something that reads as dressy from the ankles up.
These are wonderful for the office because they give you the comfort of jeans with the polish of slacks. And pointed flats are so much kinder to your feet than heels while still looking sharp. My kind of compromise.
Monochrome Trousers With Long Coat
Wearing one color head to toe, monochrome dressing, is the easiest way to look tall and pulled together. Monochrome trousers with a long coat in the same shade creates one long, uninterrupted line that is very flattering.
I do this in a soft gray or a deep chocolate. So elegant. The long coat adds drama and the matching trousers keep it clean. People will think you hired a stylist. You did not.
Printed Column Dress With Heels
A column dress falls straight and skims the body, and in a bold print it becomes the entire outfit on its own. Add heels and go.
I saved this one for last because it is my absolute favorite. When my collection of plus size work outfits felt stale, a good printed column dress was the thing that made me excited to get dressed again. One piece, one great print, and you are ready to take on whatever the day throws at you.
